Upping the Ante
My mom and I bet on everything. Whether it’s the winner of a sports match to who is going to win Wheel of Fortune or if the next traffic light we hit will be red or green. If it is something that has a definite winner, then we’ll bet on it. I don’t mean for money either. It could be for points, it could be for chores—loser has to take out the garbage!
Really big events, like the Superbowl or the winner of American Idol or whatever, then the stakes could be much higher, like doing the other person’s laundry for a week. I’m twenty, she’s forty. We share a two bedroom apartment (three rooms really, but the other bedroom is just filled with junk leftover from mom’s divorce from my stepdad five years ago).
I haven’t had a steady girlfriend since high school and mom’s been very resistant to dating since that whole stepdad fiasco. That’s way too long of a story and just not interesting enough to tell, really. That’s enough about my exciting background.
I’m writing this now because this whole betting contest my mom and I have between us started going in completely unexpected directions, and that’s why I feel the need to share what happened between us. It’s so crazy and cool, I almost don’t believe it myself, and I probably wouldn’t have if it hadn’t happened to me personally. So, let me go back to where it really started…
I can’t remember if it was November or early December, but I do remember that we were watching a Steelers vs Packers game (my mom’s always been competitive and she’s totally into all kinds of sports except golf).
I had picked the Steelers because I’d lost the previous bet, whatever it was (the previous loser always got to pick first next game/match/bet) and the bet was fairly simple—the loser had to make the winner dinner of whatever the winner wanted. At halftime, my mom was acting pretty cocky. The Steelers were pathetic during the first half and had only scored a single field goal, while the Patriots had 17 points.
She kept berating me and taunting me with all sorts of extra things that she wanted with dinner, like fresh steamed asparagus (which we didn’t even have any fresh asparagus) and other stuff like that, and that I may as well get started on it right then.
“White rice?” She mused. ”No, no, I want brown rice, also steamed, of course, seasoned with cilantro and lime.”
“Steelers are only down by fourteen, you know. That’s completely doable.”
“Not with the way they’re playing tonight, Mikey. They suck. SUCK!”
“Steelers haven’t had a three point game all season,” I reminded her, “they’ll definitely have a comeback in the second half.”
“Yeah, right. My ass they will. Oh, and with the grilled chicken, some roasted garlic cloves, yes, I can already smell them cooking…”
“Your ass, eh mom? Are you willing to bet your ass that the Patriots will hold onto that massive fourteen point lead and win the game?”
“Oh, I’m hearing a lot of talk from mister big-shot-three-point-first-half Steeler fan here! That’s all you have is talk because you know your little Pittsburgh Squealers ain’t gonna win this game!”
She certainly was confident and smug, wasn't she?
I was getting a little riled up at her smack-talking my Steelers so I said, “Fine. Are you willing to put your ass on the line then?”
“You looking to up the ante then, hot shot? I’ve got this game in the bag. You go right ahead and up that bet then—what’s your stakes now then, big guy?”
“Alright then,” I said, coming up with a really good one that would certainly shut her up, “if the Steelers make a comeback and win this, not only do you have to make me dinner tonight of my choice, you have to do it completely bare-ass naked!”
Her eyes first went really wide and then she doubled over with laughter, “That’ll be the day!”
“See, I knew you weren't willing to literally put your ass on the line because you know I’m right—the Steelers will come back to win this.”
“You…you’re serious about this bet then?” She stopped laughing and eyed me suspiciously.
“Oh, yeah. I knew you were all talk and no walk too.”
She thought for a moment then said, “Alright then, I’ll take that bet. Same stakes for you too, then. I get a naked waiter with my dinner tonight! Don’t that beat all?”
“Oh, not just serving dinner, but making it and eating it too!”
“Cool with me! You’d better start taking off your clothes and cleaning up then, too. I don’t want to be finding any stray pubic hairs in my rice now, y’hear?”
“Mom! Jeez! I’ll have you know that I keep myself well-trimmed, thank you very much!”
“Well, you won’t have anything to worry about me then either.”
“Oh, because you’re so absolutely certain you’re winning this bet?”
“Well, yes, that and…uh…you know that age old question, ‘Does the carpet match the drapes?’”
I chuckled and said that I did.
“Well then, Michael, let me put it this way: my floor doesn’t have any carpet at all on it. I’ll just leave it at that.”
“Nice one, mom!”
“As if I even needed to share that with you because I’m not losing this bet. My Patriots are going to make creamed spinach out of your Steelers anyway. Hmmm…I wonder if creamed spinach goes well with steamed asparagus anyway…”
“Dream about that all you want. My Steelers are going to knock the pants off the Patriots—oh, and you too as a result.”
“We’ll just have to see about that. In the meantime, you may as well turn the heater back on.”
“Oh yeah? You cold?”
“I’m fine, I just don’t want my son to freeze his cute naked rear end off making me my dinner tonight!”
“Riiiiight. Oh look, third quarter is just about to start…”
The impossible happened. My Steelers came back to beat the Patriots 27-24. She was still smack-talking all the way to the end of the game too, saying that her Patriots would easily make that 45-yard field goal to tie the game then win in overtime. Guess what? They didn’t! They totally botched it!
As the final seconds counted down to zero, I was up and jumping around the room with glee at winning a major bet between us, and all my mom could do was stare at the screen blankly—without any hint of an expression on her face. I’m sure that if the people were home downstairs, they would have been annoyed by my victorious stomping. My mom just shook her head, still staring at the TV screen and the talking heads wrapping up the details of the game.
“How did that happen?” she said, sounding stunned.
“Your Patriots just weren't as good as you thought they were. Oh, I can taste that steak already!”
“Alright, alright, so I need to thaw out the sirloins from the freezer. You also said baked potato, right?”
“Yep, and corn or green beans, whichever we have is fine. Don’t forget about the most important detail…”
“You have to do it all completely naked.”
“Oh come on, Mike, you weren’t really serious about that detail now, were you?”
“You bet I am—as in, you literally bet on it! You know the rules. If you agree to a bet, you can’t back out of it when you lose.”
“I only made that bet because there was no way I could lose!”
“Ah, but you did lose, which makes this victory for me all that much sweeter!”
“I can’t amend the stakes now just a little bit? I’ll make you dessert too!”
“Nope, a bet’s a bet. You lost and now you have to pay the price!”
“Alright, alright. Let it be known that Anne Nedermeyer never reneges on a bet, no matter how demeaning or embarrassing…”
“Or bare-assing,” I interrupted.
She just glared at me, half amused and half bewildered.
“Fine, fine, but if I hear one single derogatory comment about my bare ass, you’re on the next flight to Siberia, got it?”
She took a deep long sigh and then stood up and said, “Well, shit. I better go clean up then.”
“Don’t take too long! I’m starving!”
She flicked on the heater as she walked past the thermostat on the way to her bedroom.
About ten minutes later, she came out dressed in her bathrobe and slippers.
“Can I at least wear my slippers? The linoleum in the kitchen is cold.”
“Well, as long as the rest of you is completely naked, I’d be okay with slippers. The bathrobe has got to go though.”
“Yeah, yeah, I figured as much.”
She scrunched her face up into a slight grimace.
“Hey, be glad I agreed to the slippers,” I said, stifling a triumphant smirk of my own.
“Oh, you’re such a humanitarian. That doesn’t stop the fact that you tricked your mother into making you dinner—naked—and in the heart of winter no less!”
I couldn’t help but chuckle.
“Mom, winter doesn’t start until closer to Christmas. This is still fall.”
“That doesn’t stop it from being cold now, does it?”
I walked over to the thermostat.
“It says it’s 70° in here. Once you have the oven and the burners on, you won’t even be close to being cold.”
“I’ll still be naked!”
“Big deal! It’s not like I bet you to walk naked around the outside perimeter of the apartment complex.”
“That could get me arrested! You know illegal bets are off limits!”
“Exactly! It’s perfectly legal for you to be naked in the safety and comfort of your own home.”
“Well, here, I’ll at least get the oven broiler warming up then too.”
“I’m fine with that, but you can’t start touching or preparing any of the food until you have that robe off.”
She scowled at me accusatorially.
“Are you planning on watching me the whole time, or what?”
“Oh, most definitely. I have to see for myself that you are following every step of the wager, so that means that I have to closely watch you every second of you making, serving, and eating dinner.”
“What? You’re going to be in here with me the entire time? That’s just not reasonable.”
“Oh no, I’m going over here and pulling up a chair from the dinner table that I’ll sit on and watch you the entire time, verifying that you are indeed completing the bet properly.”
She rolled her eyes and sighed again.
“Fine, fine. Me and my big mouth. Here,” she said as she untied her bathrobe and quickly removed it before tossing it to me, “you can even guard my only protection and let me have it back once you feel I’ve completely fulfilled every aspect of this stupid bet.”
My mom’s face was flushed with embarrassment, but otherwise once I’d caught the bathrobe and folded it up on my lap, I was able to see a very pleasant sight. My mom wasn't thin by today’s harsh standards, but she certainly wasn’t fat either. She had a small pooch at the base of her belly that stuck out a little, her butt wasn’t athletically toned, and her nice-sized boobs drooped somewhat, but otherwise, she looked mighty fine for a 40-year-old woman. She shouldn’t have been ashamed of that body of hers for an instant.
I hadn’t noticed it before then, but I could tell that I was starting to sport a little wood at the situation. Oh, and she was right about not having any carpet—her pussy was shaved bare. When she took the steaks out of the freezer, she almost bent over to get them, but then remembered that I was watching carefully (I caught a furtive glance in my direction), so she crouched down to get them off the bottom shelf instead. She opened up the pantry and pulled out two cans and held one in front of each breast before facing me.
“We have corn and green beans.”
“Either or both would be fine,” I smiled in reply.
“Green beans it is then. We’ll get enough starch from the potatoes.”
After about ten minutes of navigating about the kitchen, I noticed that she started to ease up some and relax. Rather than crouching to get pans and stuff out of low cupboards and drawers, she started bending over to get things, but always with her ass facing away from me. I didn’t mind. I liked seeing her nice, big, all-natural boobs sway and dangle as she bent over to get pans and foil and such. After about 15 minutes, she had the steaks thawed well enough to cook. I agreed to have the baked potatoes be microwaved instead to save time.
Finally when it appeared that she wasn’t nearly as self-conscious as when she started, I asked, “Still cold?”
She thought about it for a second and then said, “Surprisingly, no. I hadn’t even thought about being cold since I first started. Oh shit, the heater’s still on!”
She turned and jogged out the other end of the kitchen into the hall to check the thermostat. I liked seeing her butt bounce up and down when she did that. It actually made my cock throb a little in my pants. (I was still wearing jeans and a t-shirt.) I heard the heater click and whirr as it did when it was in the process of shutting off; my mom stepped back into view.
“It’s 75° in here now. No wonder I’m not cold!”
“Well, good,” I said happily, “no need for this then!”
With a good toss, I threw her wadded up bathrobe into the living room where it landed on the couch.
“So I don’t get to wear that again anytime soon then, is that it?”
“Hey, the bet’s only for making, serving, and eating dinner…”
“True, but there’s no need to wear anything after that unless you really, really want to.”
“Haven’t I been embarrassed enough? Isn’t that what you wanted?”
“The bet wasn't about you being embarrassed; it was about me being able to see you naked! If you want to be embarrassed at the same time, that’s your decision. I’d much rather you have fun with it!”
“Goof around, make it fun. Dance and wiggle your booty. Squeeze your boobs together and say something like, ‘You want milk with dinner?’ and stuff like that.”
She then blushed even more than she had earlier and said, “Talk about embarrassing!”
“I’m just saying. There’s no reason why you can’t enjoy yourself at the same time.”
“I’m your mother, Michael. It would be different if I was your girlfriend or wife…”
“If it would make you feel better, I’m perfectly fine with you thinking that you’re my girlfriend or my wife.”
“Michael, you’re incorrigible! Besides, that’s not part of the bet.”
My mind reeled for an instant. She would be willing to pretend to be my wife or girlfriend for a bet? Think of all the possibilities!
“Oh, all the ideas for future bets you’re giving me! Mom, you’re a genius!”
“Oh, shit! What did I say?”
“Nothing. I just had some great ideas for some future bets now! Mwaaaahaaaaa!” I laughed maniacally as I rubbed my hands together.
“Maybe I’m better off just not saying anything then,” she snorted as she went back to stirring the green beans and checking on the steaks in the broiler.
Ten minutes later everything was done and mom started bringing the food to the table. I moved the chair back around to face the table, yet I still watched her doing everything. I would have offered to help, but part of the bet was serving the winner as well, so I planned on enjoying every second of that as well. I hoped that she’d brush up against me or inadvertently flop a boob in my face as she put food on my plate, but that didn’t happen. She was very careful and calculated in her movements.
“Mmmm! Looking good, mom!”
“Well, thank you, at least you’re appreciative…”
“The food looks good too!”
“Michael!” Her voice was stern, but the smirk on her face was even more telling.
“What kind of pervert have I raised that wants to see his own mother naked and working in the kitchen?”
“Hey, you didn’t have to agree to the bet, you know. Besides, I could have easily lost that bet and you’d have to watch my cock instead, flopping around all over the place as I served you your winning dinner.”
“I wouldn’t have been so smug about it.”
“Oh, sure you would have. You would have taunted me every second of the way while here I am, complementing you at every turn, saying how sexy you look…”
“What’s that?” She paused and looked at me.
“Oh, nothing,” I tried to correct myself, “I was saying how tasty everything looks.”
“Noooo, you said something about how sexy I look. I don’t remember you saying that before.”
“Come now, mom, you know you are quite attractive for…”
“For? For what?”
“For a mother of a healthy adult son…” I was starting to lose my words, so I grabbed my glass of water and took a sip.
“Michael,” she said demurely as she leaned on the table next to me, “did you get turned on watching me?”
“I can neither confirm nor deny that statement,” I said, taking another sip of water, “boy, I sure am thirsty tonight!”
“Did you get a hard-on watching your naked mother working in the kitchen?”
“I plead the fifth, your honor—you know, I think I’m going to need some more water…”
“Mmm, I’ll get some more water for you, my sweet bibidi,” she said, taking the glass out of my hand and rubbing my arm with the back of her other hand intentionally. She hadn’t called me her sweet bibidi in quite some time. I couldn’t even remember where she came up with that term in the first place, but she always used it in a loving reference. Why the sudden change in her?
She went from being annoyed at me teasing her to being somewhat sultry instead, practically at the drop of a hat. It seemed the change happened at my mention of the word ‘sexy’ somehow. She brought me more water and then tousled my hair playfully.
“Ah, thanks, mom.”
“No, thank you.”
I swallowed funny and started to cough.
“Why are you thanking me? You have to do all the work,” I said between getting the phlegm out of my throat. I had to take yet another sip of water to calm my coughing.
“Come now, mother dear. You went from being annoyed one second to being all loving and ‘my sweet bibidi’ the next. What’s up?”
“Well, I finally realized what your motive was for this otherwise humiliating contest.”
“You wanted to see me naked not to embarrass me, but because you thought I was sexy and knew it would turn you on.”
“So, you’re actually happier thinking that I’m viewing you as sexy eye-candy?”
She laughed deeply and said, “As odd as that sounds, I’m rather flattered, actually.”
“Well then, here’s to the sexiest mom in town,” I held up my glass which made her have to quickly set down the bowl of green beans and pick up her own glass to meet the toast.
“Cheers!” She clinked into my glass, her smile from ear to ear.
Who knew that this silly naughty bet of ours would not only get me dinner, a fun nude display of my rather sexy mom, but also make her surprisingly happy in the process? Wow! I certainly wouldn’t have bet on that outcome!
We had a wonderful dinner, with us eating and chatting about all sorts of stuff, and her in much better spirits than if I hadn't come up with that salacious ante-upper that I did and instead done all of this with the both of us fully clothed. She would have still been grumpy at losing and not getting to have her chicken with cilantro and rice. What an eye-opener!
“Ah, delicious dinner, mom! I must say, this has been the best winning bet between us that I can think of.”
“You should be glad that I’m not cold, or else I might not be in such a good mood!”
“Alright, you have fully satisfied the conditions of our bet, with an A+ for effort and attitude, by the way.”
“Well, I’m glad you feel that way!”
“I will be the charitable winner and clean up the table as well as do the dishes.”
“I must say, that is mighty sporting of you, sir!”
“I welcome you to remain in such a lovely state of undress for the remainder of the evening if you find it comfortable, but if you don’t and feel the need to don oppressive garments designed by evil men to trap and shackle the freedom that women throughout the world strive to achieve…”
“Just a tad overdramatic, are we?”
“Well, that was me saying I’d love to still see you naked, but if you feel like you have to get clothed again, I’ll understand.”
“That is mighty considerate of you, sir.”
“Ma’am!” I tipped my invisible hat as I began to clear the table.
While I was doing the dishes, she went back into her bedroom and put a different set of clothes on, more comfy lounge-around clothes like a pair of sweatpants and a long-sleeved style t-shirt. I was slightly disappointed, but I figured that’s what she would have done no matter what. I was just glad that my bet turned out as well as it did. Considering it did go so well, maybe, just maybe, I could raise the stakes next time?
Well, the next two games we watched that week, I tried making a play on the nudity clause again, and she was fine with making the bets, but I lost both of them! One bet was to clean the bathroom naked, which I thought would be awesome to watch my mom do that, having to do a lot of bending over and what not, but I lost that one and I had to clean the bathroom naked all by myself. She didn’t watch me doing it at all and she tended to stuff in her bedroom instead, so I was definitely more than a little bummed out at her lack of interest.
The next one, I bet on naked dinner again but I lost that and instead of watching me, she read one of her celebrity magazines in the living room while I cooked. I rubbed my dick all over her plate before I put any food on it without her seeing me just out of frustration (don’t worry, I checked to make sure I didn’t leave any pubic hairs). While eating the chicken dinner that she had wanted on the night where I won the nude dinner bet, I asked her why.
“Alright mom, why do you accept these nude bets when you don’t care about watching me perform naked as part of your winnings?”
“I do that more for your benefit now than anything, Mike.”
“It’s my benefit to be naked?”
“No, it just seems to make you happy at the thought of possibly seeing me naked somehow as part of your winnings, and I’m okay with that.”
“But not vice-versa?”
She sighed and said, “Honey, I’ve seen you naked ever since you were a baby. You don’t have anything that I haven’t seen before. Evidently you’re feeling so deprived of seeing a naked woman in the flesh, that you’re even willing to be aroused at the sight of your own naked mother.”
“I wouldn’t put it quite like that…”
“Besides, let’s say that I was equally titillated at the sight of your naked body, where would that put me?”
“Uh, in a state of sexual arousal?”
“Well, yeah, but I’m your mother, Michael. You’re my son. It’s natural for a boy to desire to see women naked, that’s just human nature…”
“Mom, I’m a man. I’m twenty years old. I can get married, I can go to war for my country. Very soon I can legally drink and gamble too.”
“Boy, man, there’s really not much difference, actually. You were more mature at 15 than many men are at 50.”
“Am I not attractive to you then?”
“That’s not it at all, and you know it. You’re a very handsome young man. If I was younger and not your mother, I’d probably be all over you in a heartbeat. I wasn't exactly little-miss-goody-goody when I was your age. Boy, if your grandfather knew what I was getting into when I was twenty, he’d have died ten years earlier than he did!”
I smirked and replied, “Well, then what about being at your age now and you weren’t my mother? I have a thing for older women, you know.”
“Just what are you trying to get at? I am your mother, there’s no escaping that. Are you asking if we were roommates here and not related, would I be acting any differently?”
“If I was a single 40-year-old horny cougar and you were my single 20-year-old boy-toy roommate?”
“Yeah, what then?”
“Well, all I can say is that there wouldn’t be anything holding me back then.”
“So the age difference wouldn’t be an issue to you?”
“Look, Michael, are we having this conversation because you want my permission to date an older woman? If so, this is a really strange way of going about it.”
“No, no, that’s not it at all…”
“If it is, that’s fine with me. If you’re attracted to older women, that is completely fine. I would have thought you’d be more interested in girls your own age, but if you…”
“Mom, please, that’s really not what I’m doing here.”
“Then what is? Other than teasing me with all of this sexy talk and acting like you’re attracted to me…”
“But I am attracted to you!” I blurted out.
“That’s wonderful, Michael, really, it is, but I’m your mother…”
“What if you weren’t?”
“But I am! It’s not like you can win a bet and change reality in the process.”
“I don’t want to change reality. I still want you to be my mother.”
“But you’re acting like that’s not good enough, that you’d rather me be your 40-year-old girlfriend instead.”
“I never thought nor used the word ‘instead’ here at all.”
“I love that you’re my mother, I would never want to change that.”
“Then all you’re doing is confusing me.”
“I’m just saying that maybe, sometimes, it might be fun, to pretend if you will, that we weren't related and maybe do some fun things with each other that…”
“Michael, stop,” she said firmly.
She swallowed and took a deep breath before saying, “Are you…are you talking about incest here?”
I winced, knowing that the tone of voice she used was one of her most deeply serious ones that she’d ever used on me.
“I…uh…” I didn’t know what to say.
I couldn’t try to come up with some lame excuse because that’s exactly what I was trying to lead the conversation to and around, without saying the word of words. I sheepishly looked down at my own half-eaten plate and suddenly felt like my stomach was already filled with rocks.
“Is it?” She asked, her voice slightly higher, yet still highly inquisitive.
“I’m, I’m sorry,” I said, still looking down at my plate, ashamed at myself for doing and saying what I did, “I’ll stop with the whole naked bets.”
“Michael, Michael,” she said more soothingly, “please, tell me, honestly. You’re not in trouble.”
“I don’t know what to say.”
“The truth would be nice. There’s no need for you to be cryptic or beat around the bush anymore. Has this been about incest the entire time?”
“What would happen if I answered in the affirmative?”
She snorted and said, “You’re not under trial here, Michael. If you are sexually attracted to me, just go ahead and tell me!”
“I thought you already knew that?”
“I…” she sat back in her chair and looked both stunned and introspective, “I…sort of guess I did, but was convincing myself that it was something else…”
There was a long silence. I just picked at my food, but my mom continued to eat with a somewhat bemused look on her face.
I couldn’t take the pressure anymore and cried out exasperatedly, “What?”
“Okay, if you had the chance to have sex with me, would you do it?”
I could feel the blood rushing to my face and I couldn’t look her in the eye, “I…I don’t know how to answer that…”
“Oh, a simple yes or no would suffice.”
I exhaled sharply.
She cupped her hand to her ear and said, “What was that? I couldn’t hear you.”
“There! That wasn't so hard now was it?”
“Delicious dinner, honey! Very informative too!”
She smiled and winked as she took another bite of rice before setting down her fork.
“So…what’s for dessert?”
“Are…are you mad at me?”
“For wanting some dessert?”
“No, no,” I said and swallowed heavily, “for the whole realization of my sexual attraction to you.”
“Why should I be mad at that? I’m actually honored.”
“I…uh…couldn’t really tell. You sounded scarily serious when you mentioned the I-word.”
“You mean incest?”
“Uh…heh…that would be the one.”
“I had to be sure you were for real.”
“What? Why wouldn’t I be for real?”
“Well,” she said as she took a sip of water, “I originally thought this was all about humiliation or gloating more than anything.”
“Why would you think that? Didn’t I convince you otherwise on the night where you made me dinner naked?”
“I guess I just blocked out thinking it was for arousal purposes. I mean, I knew you liked seeing me naked, but I still thought it was more of a ‘Haha, I won and now you have to be naked!’ sort of thing rather than a ‘Damn! My mom’s hot—I would so totally fuck that!’”
“Mom!” I gasped and instantly started to blush.
“Well, doesn’t that pretty much sum it up?”
I didn’t have an answer for that. She had rendered me speechless for once.
“Does it?” She looked at me inquisitively.
I sort of shrugged while nodding sheepishly and looking down at my plate.
“Alright then,” she exhaled, “what’s for dessert?”
“Works for me! I’ll take Rocky Road if we still have some.”
“Yeah, I think we do. I haven’t touched it.”
“Two scoops, please!”
“Shouldn’t I clean up the dishes first?”
“Nah, bring me some ice cream and I’ll help you clean up afterwards.”
“Alright,” I said as I went into the kitchen in the quest for frozen dairy delights.
Sure enough, there was some Rocky Road and it was still about half full. There was also some vanilla ice cream that was covered in a thick layer of freezer frost that I decided would be better suited for the garbage can rather than a dessert bowl. I scooped up two generous scoops of Rocky Road and brought the bowl to my mother.
“Hey! What about whipped cream?”
“Do we have any?” I asked.
“I think we do. Check the door.”
I opened up the fridge, and sure enough, there was a can of whipped cream on the bottom rack of the refrigerator door. I grabbed it and took it over to my mother as she waited patiently at the table with her untouched bowl of Rocky Road in front of her. I held the can out to her but she didn’t take it from me. Instead, she looked to the bowl in front of her, raised her eyebrows and then looked back at me expectantly. I sighed and chuckled, which made my not-so-soft cock bounce up and down a little and I caught her giving it a quick glance before looking back at her ice cream.
“Say when,” I said as I shook the can and began dispensing the frothy cream atop its frozen cousin.
“That’s good.” She said when I had the top of the ice cream well-coated.
I sprayed some in my own mouth for good measure too. I mean, who can resist whipped cream from a can? I sure can’t.
I was about to put the cap back on the can when she said, “What about me?”
She looked to me and opened her mouth wide.
“You want some too?”
“Uh-huh,” she said, keeping her mouth open the entire time.
The thought went through my head of putting something else in that open mouth of hers instead of whipped cream and it made my cock instantly twitch. I shook the can again and I could feel my cock get even harder, not able to remove the sexier thoughts that were permeating my brain. Well, you’ve got to consider my situation there. We had just had a mildly sexy talk that involved incest, I was naked, and standing next to my mom with her mouth open and looking all sexy. I sprayed the can into her mouth and she laughed because it filled up much faster than either of us expected. Some creamy flecks sprayed back out of her mouth and landed on me as she managed to swallow the rest of it.
“That’s good stuff!” She laughed.
“Now it looks like you want to put something else in my mouth instead!” She winked.
“Yeah, I’ve got something else that dispenses cream too.”
“Nice!” She laughed and snorted.
“Well, you said it first!”
“Here, here, give me the can…”
“Why?” I asked suspiciously.
“Just give it to me.”
I handed the can of whipped cream over to her reluctantly.
“Okay, stand still.”
“Uh…what are you planning?”
“Just don’t move.”
She took the can, gave it a few more shakes, and then proceeded to carefully spray some whipped cream on the tip of my hard cock.
“I like where this is going!” I said, delighted by the impending possibilities.
“There,” she said proudly, “now he looks like Santa Claus!”
“Ho ho ho!” I said.
“If we only had a little red Santa cap!”
“Want to sit on my lap, little girl?”
My mom snorted again as she reeled back in her chair laughing.
“Oh, Santa, I always wanted to visit the North Pole,” she said, still laughing.
“Well you’re in luck, I AM the North Pole,” I said with another trio of hoes.
A dollop of whipped cream fell off the side of my cock and splattered on the rug.
“Stay right there!” She commanded and I froze still.
She leaned over and took the head of my penis in her mouth and deftly slurped off all the whipped cream in the flash of an instant.
“I couldn’t risk you dripping any more on the rug,” she said calmly as my heart was racing.
Did she just suck whipped cream off the end of my dick? Did that really just happen, or did I imagine that?
“I can put some more on it if you like?” I said, awestruck by her action.
“Some other time maybe, quick get a paper towel so it doesn’t stain the rug.”
I grabbed one from the other end of the table and crouched down to clean up the drip, my heart pounding and my cock throbbing relentlessly. I was in a state of dazed shock as my mom proceeded to eat her ice cream and smirk at me repeatedly as I, passing on the ice cream myself, stayed busy by putting stuff away and cleaning off the table despite her offering to help me after she finished eating. My cock remained rock hard the entire time!
“I did say that I’d help you clean up, you know,” she said as she finished her last bite of Rocky Road, the whipped cream long gone.
“Well, now that you mention it,” I retorted, “I do think there’s still a little bit of whipped cream left on this that you could clean off…”
My cock was completely clean of whipped cream, but it was starting to get a little drippy with pre-cum in all of my excitement.
“Nice try, bucko,” she grinned, “but I’ll remind you that I was the one who won the bet.”
“Oh, so if I was the one who won the bet, you’d be willing to do more than lick some whipped cream off it then?”
“Well then, I’d have been the one naked and you’d have been the one clothed.”
“You could be naked right now too, you know.”
“Oh, I suppose I could, but I reiterate—I was the winner!”
“Since you won, then why didn’t you spray whipped cream on your pussy and have me lick it off then?”
Oh shit—she sounded legitimately shocked. Had I crossed a line? Fuck! She sucked whipped cream off the end of my cock, for Christ’s sake!
“I’m just saying, is all. That would be your right as the victor…”
“You naughty boy!”
She sounded less mad then, and more than a little impressed.
“You’d really do that?” She looked at me with an expression that I took to mean represented both interest and incredulity.
“You bet I would!” I smiled as I felt a drip of wetness fall off my cock and land on my foot.
“Well, alright then, I think I know what our next bet will be…”
“What? You mean we have to wait for another betting opportunity?”
“Well, yeah, that’s a pretty big step in this whole thing, don’t you think? I think that should wait until we have another big bet.”
I wasn't willing to wait that long. I was so turned on that I either wanted her to suck my cock or have me eat her pussy.
“All right, I’m upping the ante then,” I said as I grabbed a dime off the kitchen coin plate.
“Heads, you suck whipped cream off my cock; tails, I lick whipped cream off your pussy.”
“Hold it, hold it,” she said, “You’re not upping the ante. The game’s over and I won fair and square. Besides, I’m too full of ice cream to want to lick up any more whipped cream.”
“Well, you can simply pretend that my cock is covered in whipped cream then as you’re licking it.”
“You’re missing the point that I’ve already won and you’re too late to up the ante.”
“Well, I didn’t know oral sex was a possibility while the game was still on!”
“Well, I didn’t either!”
“Okay, mom, you won fair and square. I didn’t have any dessert, so as part of your winnings, you can have me lick whipped cream off your pussy.”
“Huh? What did you say?” I was still coming up with a plan of attack so I completely missed what sounded like her agreeing to my offer.
“If you really mean it, you can lick whipped cream off my pussy.”
“Only if you’re serious and this isn’t just one big joke.”
“Oh, when it comes to licking pussy, I am deadly serious!”
“You’d better be, young man! You have me more turned on right now than I’ve been in ages!”
“Shit, I’ve been getter wetter by the minute as I ate my ice cream thinking about how naughty I was with your dick and all.”
“Well, I’ll grab the can then. Where would you like your bonus winnings performed?”
She thought for a second and said, “Let me go clean up and then you can come into my bedroom. It may as well be on my bed. Give me a few minutes.”
“It’s a deal!”
I finished picking up the rest of the dishes as she trotted off to her bedroom. I heard the sound of the shower turning on, so when she said she wanted to clean up first, she really meant it! I’d better not disappoint! I kept the can in the fridge until I heard the shower go off. I grabbed it and quickly headed into her room and sat on her bed.
I had been naked for almost two hours by that point, and my cock was as hard as it had ever been, just thinking about not only getting to see my sexy mom naked again, but I was surely minutes away from eating her pussy covered in whipped cream! I’d have to say that this bet turned out to be a win-win after all! She came into the bedroom wrapped in a white towel, with her hair still wet and dripping on her shoulders.
She smiled at me and said, “Looks like you’re raring to go!”
“You bet I am,” I grinned.
“So you’re really serious then? You want to spray whipped cream on my…um…you-know-what and lick it off?”
“And anywhere else on your body that you want me to spray and lick!”
“Well, okay then!”
She took off the towel and rang her hair out with it to try to get as much water as she could. She hung up the towel on a hook and said, “So, where do you want me?”
“Well, I suppose lying down on your back on the bed would be a good start!”
“Alright, get up so I can pull back the sheets. I don’t want to get anything on the comforter.”
I promptly stood up and she pulled the bed covering back revealing her blue and white striped sheets beneath. She then propped up her pillow and first sat down on the bed, her large boobs hanging naturally and tantalizingly.
“You don’t have to do this, you know. It wasn’t part of the original bet.”
“Pish-posh! You deserve it, mom! Besides, this is the most excited that I’ve been in ages!”
She shot a glance at my throbbing cock, with juice beading up at the tip and said, “I see that!” She pulled her feet off the floor and laid flat on the bed with her legs together. I climbed up on the edge of the bed below her and waited for her to spread her legs but she remained still. I gave her a curious, expectant glance.
“I can’t very well eat whipped cream off your pussy with your legs together now, can I?”
“I thought you’d want to spray some here,” she motioned to the spot on her crotch where her pubic hair would have been if she’d had any. It actually looked like she’d just freshly shaved. I couldn’t see a trace of pubic hair or even a hint of a bristle.
I shrugged and said, “Alright.”
I crawled up onto the bed on my knees next to her with the can of sugary dairy product in my hand and gave it a few shakes before popping the top off.
“Ready,” she nodded.
I proceeded to spray a circular dollop of cream right at the spot where you could just make out the top of her vaginal crease.
“Ooooh! It’s cold,” she squealed.
“It won’t be for long,” I said as I popped the cap back on the can and tossed it to the side.
I immediately bent over, with one arm supporting myself on the bed on each side of her as I began to slowly lick the top of her pubic mound just below her belly.
I was at the top edge of the whipped cream and only got a small taste of it. What I could mostly taste was the clean freshness of my mom’s skin, which was quite pleasant as well.
“Oh, that does feel nice!”
“I haven’t even started yet,” I smiled as I slowly licked downwards and got more and more of the cream with each lick as I got closer and closer to her crease which was sure to be not far from her clitoris. It would have been pretty hard to get to her clit without her legs being spread, but my tongue was willing to try anyway. As I licked more and more, my mom hummed softly and sweetly as if she was finding it quite pleasant. I tried flicking my tongue down between her legs, but I couldn’t get very far. Time for me to take charge!
“Okay, spread ‘em, lady!”
“I have a job to do here. I can’t lick up all the whipped cream unless your legs are spread as wide apart as you can handle!”
“Yep. Spread those legs, woman!”
She chuckled and said, “Alright…sir.”
As she spread her legs, I took up a new position between them as I proceeded to lie down on my stomach and prop myself up by my elbows. I was getting the best view of her pussy ever, unless you count the time I came out of it some twenty years ago! Wow! For a forty-year-old woman, her pussy looked amazing!
“Oh, I see what your problem is,” I said, acting all concerned.
“What?” She said lifting her head up with a worried look on her face.
“Spread your legs wider so I can see better.”
She did and even used her arms to hold them back.
I gasped and said, “You’re missing something!”
“Missing something? I just shaved. Do you mean pubic hair?”
“No, that’s not it…Oh! I know!”
With surprising speed, I quickly sprayed a huge line of whipped cream from the can I had surreptitiously hidden from her view. She most likely thought it was still where I had tossed it, but I had sneakily grabbed it while we were adjusting positions and had quietly popped the lid back off! She shrieked with delight at the sudden spray of cold dessert topping that went in a line right down the middle of her labia and it immediately started to slide before I had a chance to start licking again. By the time I had the cap back on and the can tossed to the side, the whipped cream had slid as a mass about an inch downwards with the lowest part covering her asshole.
“You bad boy! You had me scared there for a second!”
“You can spank me later,” I snickered.
“I feel it running down. You better not let any drip on the sheets!”
“Oh, I won’t!”
I quickly slid forward and caught the lowest part of the whipped cream that was about to run past her asshole and drip on the bed. I slurped up the dollop of cream and continued to lick around her asshole.
She gasped in surprise and said, “Mi…Michael, you…you know that’s my asshole, right?”
“Of course I do. It’s clean isn’t it?”
“Of course it is! I just showered!”
“Then rest your head back and let me do my job!”
With that, I licked her asshole even more passionately and she threw her head back against her pillow and moaned with shock and delight.
“My god, Michael, I had no idea that you were this kinky! I’ve never had my asshole licked like this before!”
“Mmm,” was all I could say since my tongue was busy circumnavigating my mom’s asshole. Every so often, I would quickly lick up some more of the cream as it dripped down, but I was really enjoying giving my mom her first rimjob. It seemed like she really enjoyed it simply because she stopped talking and only panted and moaned with pleasure. It was time for me to step up my game a notch. After giving her rosebud a few more licks, I repositioned my head to start getting the last remnants of whipped cream and I began to probe my tongue deeper and deeper into her vagina.
“Oh my god, Michael, I had no idea!”
I licked and probed as deep as my tongue would go before licking upwards to her sensitive clitoris. I found it less by the feel of that familiar bump and more by the gasp and shuddering that my mom went through before saying, “Oh, baby, you found the spot!” Sensing that this was what she really wanted, I continued to lick her pulsating little bean as she gasped and moaned louder than before.
With my left hand, I was able to pull the clitoral hood of skin up to completely expose her clit to my tongue as I flicked over and around, slow at first, but then continuously building up speed as I essentially performed the Mexican hat dance on my mom’s clit with my tongue.
“Oh, baby, keep doing that! Don’t stop!”
I continued and only increased my pace as she began to buck up and down as she panted heavily.
“Oh, oh, there it goes! I’m coming, baby! I’m coming!”
With that, she released her grip on her legs as she began to twitch and shudder beneath my ravishing licks as her orgasm overwhelmed her. She even grabbed my head and forced it hard into her pussy as she came, making it hard for me to either breathe or lick, but I did the best that I could which was evidently wonderful since the only noises to come out of her at that point were moans and soft cries of passion. As I could tell that her orgasm was receding, I lessened my pace and her panting and moaning slowed as well.
“Oh my god, Michael! That was amazing! Amazing!”
“I’m glad you liked it!”
“How about you? Are you still hard?”
“As a rock! I probably dribbled cock juice on your sheets actually…”
“Well, I have an idea on how you can make it up to me then.”
“Oh yeah? How?”
“Fuck me! Right here, right now!”
“Oh, yes, don’t give me time to change my mind either! If you fuck half as good as you lick pussy, that I’ve just got to have you inside me!”
I didn’t waste a moment climbing on board. My mom held her legs wide open again and I took hold of my rock-hard member, slick with its own juices, and rubbed the tip in the vicinity of my mom’s vaginal entrance where my tongue had been only moments before. She was so wet that I slid into her almost effortlessly. I began to thrust slowly into that womanly area that I had emerged some two decades before—staring down with amazement that it was indeed my cock going in and out of my mom’s pussy! I had my upper torso completely propped up at arm’s length, almost like I was doing a pushup as I continued my slow, deep pelvic gyrations.
I looked up into my mom’s face to see her staring at me with infinite adoration in her eyes. Once our eyes locked, she reached her hands up to me: one to caress my cheek, the other the rub the side of my head. I could feel her try to pull me down to be even closer to her, which I eagerly did, soon finding our lips locking as we kissed and gasped for air then kissed some more as I continued to lovingly fuck my mother. We didn’t say a word to each other; we merely enjoyed the closeness of each other’s skin, the taste of each other’s lips, and the feeling of each other’s sex simultaneously.
It was pure love and ecstasy rolled into one. I’d had sex before, but this was different. I realized that I had never truly made love to any girl before. Sure, I had made lust many times by way of fucking and cumming, but this was so much more than that. I felt it to the depths of my very soul!
Oh, and how good it felt? Simply amazing! Wet, soft, smooth, tight, caressing, all of that. With every thrust, my mom’s hips raised slightly to match and meet my cock to its fullest potential. She definitely knew what she was doing! I began to increase my pace, and she really seemed to like that idea with a wild gleam in her eye and a sexy smile spread across her face.
“Oh god, baby, this is wonderful,” was all she gasped out and I realized that it was the first words that either of us had said other than grunts and moans for a miniature eternity. I propped back up a little higher so that I could get more air as I continued to hammer deep thrusts into my mother’s warm, welcoming womb. As she breathed quickly, she began adding cute little squeals to the ends of her moans, showing me that she was really liking what I was doing.
“Oh, baby, I’m close,” she gasped as she moaned.
“I’m close too, mom!”
“Oh god, baby, right there, right there!”
I turned my focus and looked down at my handiwork, doing what I could to make sure that I didn’t cum before I could tell that she would too as I could see my cock pull almost all the way out of her pussy only to be rammed quickly and deeply back to the hilt.
“I…I’m going to cum too! Should I…should I pull out?” I wheezed as I tried to keep a level head.
“Oh, cum inside me, baby! Cum inside mommy!”
That was too much for me to bear as my own orgasm overwhelmed me and I could tell that she was lost deep in her own orgasm as well. I could feel the added slickness as my cock began to shoot and spurt deep inside my mom’s defenseless pussy. A cum had never felt so good in my life!
I could feel my mom convulse and her pussy constrict around my cock as she came, which only increased how good it felt for me in return. I couldn’t tell exactly how much I came, but it sure as hell felt like a lot! I continued to thrust even after I could feel the last spurts leave my cock as I panted and gasped as she slowly came down from her orgasm. I virtually collapsed on top of her, yet I still managed to slowly thrust into her until my cock became too soft to work with and it finally popped out followed by a sticky slurp. She wrapped her arms around me and held me tight as our breathing returned to normal.
We didn’t say anything—there wasn't anything that needed to be said. What we did was both wrong and absolutely amazing. Our relationship could never be the same again. As she held me close and rubbed my hair, she kissed the only skin of mine that she could reach, which was my forehead.
“So, how did you like your winnings,” I asked, my cheek resting on her boob.
She laughed and squeezed me tightly.
“Wow.” That was all she could say.
“Oh, baby, better than good. That was the best sex in, well, ever!”
“Well then, you are welcome!”
“So condoms or the pill?” She asked as she continued to stroke my hair.
“Well, if this is something that you only want to do every so often, I’d say we’re going to need to get condoms. If you’re up for this to be a regular thing between us, I’d be happy to take birth control.”
“Oh, shit, I totally came, like buckets, inside of you. Are you going to get pregnant?”
“No, no, my period’s going to start in like two days. There’s no possible way I could get pregnant this late in my cycle.”
“Well, shit mom, you’d better start getting on the pill, because you can bet that every bet I have with you will involve sex of some sort from now on!”
“So if you win, I have to have sex with you, and if I win, you have to have sex with me?”
“That sounds fair to me,” I said, my face lighting up with the biggest smile.
I could feel life returning back to my cock with the thought of getting to have sex on a regular basis with my hot MILF of a mom. Evidently my mom could feel my cock start to get hard again, as it pressed up against her leg.
“I have a new bet right now,” she said with a mischievous gleam in her eye.
“Yeah, I bet you can’t make me cum again before I make you cum again!”
“Oh, it is on, woman!”
For the record, I got her to cum at least three times before I came again.
How’s that for upping the ante?
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